First of all, let me state that I have nothing against GM Brian Cashman or the New York Yankees organization. I know Cashman does his best to keep a playoff-contending team year in and out.
What this is for is to just lay out the possibilities that "could have been," as the Yankees' goal towards 28th championship has officially started today.
Now, the following prospects are very hyped ones—or at least they used to be.
These guys could have been traded for superstars that could have impacted the division and put the Yankees in much better positions than they are in now.
Here is just a sample of them from Cashman's tenure...